Synthesis of Polyhydroxyalkanoates by Polymerization of Methyl 3-Hydroxypropionate in the Catalysis of Lipase

doi:10.1016/S1872-2067(11)60336-7

Abstract

Abstract: The polymerization of methyl 3-hydroxypropionate as monomer catalyzed by lipase was selected as a model system in this study. The monomer with the purity around 95% could be polymerized to polyhydroxyalkanoates in the catalysis of Novozym 435. Decreasing the reaction pressure would result in the increase of product yield and high molecular weight. By choosing appropriate organic solvents, surfactants and reaction pressure, the molecular weight of polyhydroxy propionate polyester could be controlled from 1800 to 13000 (M_w value). The reusing ability of enzymatic catalyst was comparatively good. The relative activity could be maintained above 95% after 6 repeated batches reaction.

Key words: polyhydroxyalkanoates, polymerization, enzyme catalysis, lipase, methyl 3-hydroxypropionate

SONG Hao, ZHAO Yong-Jie, ZHANG Ying-Xin, KONG Wei-Bao, XIA Chun-Gu. Synthesis of Polyhydroxyalkanoates by Polymerization of Methyl 3-Hydroxypropionate in the Catalysis of Lipase[J]. Chinese Journal of Catalysis, 2012, 33(3): 432-438.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(11)60336-7

https://www.cjcatal.com/EN/Y2012/V33/I3/432

References

1 Baki H, Alexander S. Appl Microb Biotech, 2007, 74: 1
2 Valappil S P, Misra S K, Boccaccini A R, Roy I. Expert Rev Med Devices, 2006, 3: 853
3 Chen G Q, Wu Q. Biomaterials, 2005, 26: 6565
4 Anderson A J, Dawes E A. Microbiol Mol Biol Rev, 1990, 54: 450
5 Anderson A J, Williams D R, Taidi B, Dawes E A, Ewing D F. FEMS Microbiol Rev, 1992, 103: 93
6 Chen G Q, Wu Q, Xi J Z, Yu H P. Progr Nat Sci, 2000, 10: 843
7 Byrom D. Trends Biotechnol, 1987, 5: 246
8 Choi J I, Lee S Y. Bioprocess Eng, 1997, 17: 335
9 Uyama H, Kobayashi S. J Mol Catal B, 2002, 19-20: 117
10 Albertsson A C, Srivastava R K. Adv Drug Deliv Rev, 2008, 60: 1077
11 Kobayashi S, Uyama H, Ohmae M. Bull Chem Soc Jpn, 2001, 74: 613
12 Kobayashi S, Uyama H, Kimura S. Chem Rev, 2001, 101: 3793
13 Kobayashi S, Uyama H. Curr Org Chem, 2002, 6: 209
14 Santaniello E, Ferraboschi P, Grisenti P, Manzocchi A. Chem Rev, 1992, 92: 1071
15 Kobayashi S, Shoda S I, Uyama H. Adv Polym Sci, 1995, 121: 1
16 Kaplan D L, Dordick J, Gross R A, Swift G. Enzyme Polym synth, 1998, 684: 2
17 Gross R A, Kumar A, Kalra B. Chem Rev, 2001, 101: 2097
18 Kobayashi S. J Polym Sci A, 1999, 37: 3041
19 Varma I K, Albertsson A C, Rajkhowa R, Srivastava R K. Progr Polym Sci, 2005, 30: 949
20 Dong H, Wang H D, Cao S G, Shen J C. Biotechnol Lett, 1998, 20: 905
21 Gorke J T, Okrasa K, Louwagie A, Kazlauskas R J, Srienc F. J Biotechnol, 2007, 132: 306
22 Knani D, Gutman A L, Kohn D H. J Polym Sci A, 1993, 31: 1221
23 Andreeben B, Steinbuchel A. Appl Environ Microbiol, 2010, 76: 4919
24 Liu J H, Wu H G J L T, Xu L W, Chen J, Xia C G. J Mol Catal A, 2007, 269: 97
25 Liu J H, Chen J, Xia C G. J Mol Catal A, 2006, 250: 232
26 Wehtje E, Adlercreutz P. Biotechnol Bioeng, 1997, 55: 798
27 林智健，李光吉，龙俊元，宗敏华. 催化学报(Lin Zh J, Li G J, Long J Y, Zong M H. Chin J Catal), 2011, 32: 123

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